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Coed Tuscany Gravel Bike Retreat
Pienza, Tuscany
Aug 30th – Sept 6, 2026
Cost: $3850
$950 extra for single room (email colleen@womensquest.com to check on availability)
Hello and Welcome to Women’s Quest!
While gravel riding has been around since the advent of bicycles, there is no question the Italians have perfected the art form. Tuscany is filled with thousands of miles of gravel roads, or strade bianche (white roads) that thread their way through the rich and welcoming land of postcard and calendar photos, and movie landscapes.
And we’ll be staying in the middle of it all, in Pienza, a UNESCO World Heritage site and the center of this gravel heaven. Pienza is a beautiful postcard town with phenomenal rides heading out in all directions. You may know Pienza from THAT scene in Gladiator where Russell Crowe dreams of home in the endless wheat fields. Yep, that’s Pienza. It’s also a stone’s throw from the most famous cypress lined winding road in Tuscany featured in just about every Italian based Rom-Com of late.
We’re super excited to spend a week with you exploring the famous white roads of Tuscany and experiencing the beauty, culture and awesome food and wine of the Val d’Orcia.
Please feel free to call or write if you have further questions.
With excitement and anticipation,
The Women’s Quest Staff
What Will the Riding Be Like?
In a word – heaven. We’ll be riding on the storied gravel roads of the Val d’Orcia, also a UNESCO World Heritage site and home to the famous L’Eroica old school Grand Fondo, the professional spring classic Strade Bianche and recent gravel segments of the Giro d’Italia.
We will be riding between 25 miles and 50 miles a day (it’s gravel so it takes longer) and climbing around 1,000’ per 10 miles. The riding will be a mix of paved and gravel, with an emphasis on gravel, with rolling hills interspersed with some short punchy climbs and a couple of longer sustained efforts.
Some of the towns we’ll ride through include Montalcino, Montepulciano, Montechiello, San Quirico, Buonconvento, and Bagno Vignoni (the only town with a hot springs pool as its town square.) We’ll ride by the Monastero Sant’Anna in Carpena (the setting for The English Patient) and Crete Sienese (the Sienese clay formations)
You do need to be comfortable riding gravel. While most of the gravel roads are hard packed there are some softer sections and some washboards from time to time that can sneak up on you. We really emphasize to everyone to “stay in the boat” and ride well within your comfort window. Afterall, we are here to soak in the Tuscan landscape, absorb the history of the Strade Bianche and immerse ourselves in La Dolce Vita of Tuscany.
The rolling hillsides through which we’ll ride are a mixture of vineyards (likely lush with grapes ready for the harvest), olive groves (heavy with olives undergoing their last growth spurt before harvest in early November) and newly cultivated hillsides.
All rides will be guided and we’ll likely split up into two groups so everyone can ride at their comfortable pace. We’ll also provide GPS links of the routes so you can ride solo or with a friend if you’d like to soak in the Tuscan countryside in a smaller setting.
What’s Included?
Our adventure includes:
- 7 nights lodging at a four star hotel
- 7 big buffet breakfasts
- 6 fabulous dinners (one dinner on your own)
- Guided riding
- An optional off the bike day in either Siena or local hot spring (TBD)
- Wine tasting at a local enoteca
- Cheese tasting at the best pecorino shop in town
What’s not included:
Airfare, transportation to Pienza (although we may be arranging for a transfer from Florence), lunches (which will be on your own during the rides), bike rentals (however, we will arrange them – including e-bike options!)